Trifluoroacetic acid → HCID 25109291, compound

HRID 2059719Notes

Reaction equation

HRID 2059719 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)[C:9]2[CH2:8][CH2:7][C:6]3[O:25][C@H:26]4[CH2:31][CH2:30][CH2:29][CH2:28][C@H:27]4[C:5]=3[C:4]=2[N:3]=1.FC(F)(F)C(O)=O>>[N:12]1([C:10]2[C:9]3[CH2:8][CH2:7][C:6]4[O:25][C@H:26]5[CH2:31][CH2:30][CH2:29][CH2:28][C@H:27]5[C:5]=4[C:4]=3[N:3]=[C:2]([NH2:1])[N:11]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68801968HCID 68801968, compound

Product 1

HCID 25109291HCID 25109291, compound

Procedure

The product from Example 3A (179 mg, 0.419 mmol) was cooled with an ice bath and treated with trifluoroacetic acid (6.5 mL, 84 mmol) for 1 minute, then concentrated under reduced pressure for about 2 minutes to remove excess trifluoroacetic acid. The residue was cooled with an ice bath, taken up in dichloromethane (50 mL) and basified with sodium hydroxide (10%). The organic layer was separated, dried with magnesium sulfate, and concentrated under reduced pressure. The resulting residue was chromatographed on a silica gel column eluting with ammonium hydroxide/methanol/dichloromethane (0.8/8/92) to provide the title product in enantiomerically enriched form: 1H NMR (CDCl3) δ 1.20-1.31 (m, 2H), 1.44-1.53 (m, 1H), 1.53-1.61 (m, 2H), 1.71-1.85 (m, 1H), 2.08-2.16 (m, 2H), 2.42 (t, 2H), 2.67-2.78 (m, 2H), 2.93-3.00 (m, 4H), 3.03-3.10 (m, 1H), 3.10-3.16 (m, 4H), 4.62-4.69 (m, 3H); MS (DCl/NH3) m/z 328 (M+H)+; [α]58920−106° (c 0.0038, methanol).

Workup

  1. concentrationconcentrated under reduced pressure for about 2 minutes
  2. customto remove excess trifluoroacetic acid
  3. temperatureThe residue was cooled with an ice bath
  4. customThe organic layer was separated
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was chromatographed on a silica gel column
  8. washeluting with ammonium hydroxide/methanol/dichloromethane (0.8/8/92)

Sources & evidence

ORD record
ord-be628f71eb7e4b32ae20ffa006d839de
Source dataset
uspto-grants-2012_10
Patent number
US08278311B2

Reaction notes

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